


First Time

by Angelicfall67



Category: Supernatural
Genre: Bottom Dean, Dirty Talk, First Time, Fluff, M/M, PWP, Top Sam
Language: English
Status: Completed
Published: 2014-11-08
Updated: 2014-11-08
Packaged: 2018-02-24 13:22:35
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,823
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2582930
Author URL: https://archiveofourown.org/users/Angelicfall67/pseuds/Angelicfall67
Summary: <blockquote class="userstuff">
              <p>It's Dean's first time. Sam intends to make it good for him. </p><p>Prompt for Dean having his first time with Sam.</p>
            </blockquote>





	First Time

The room that Sam booked was special for tonight. It was a rather nice hotel room, with clean bed sheets for once. There was a bottle of wine and a bowl of strawberries on the bedside table. The bed was a king sized, with crimson red silk sheets and the softest mattress they'd ever slept on before. Sam knew that Dean would complain that he wasn't a girl, he didn't need to be pampered but it was a special night. Dean deserved to be pampered, in Sam's opinion.

Getting checked in to the hotel was a new experience. Sam had wrapped his arms around Dean's waist, shamelessly flirting and teasing his brother until Dean was blushing from what Sam was whispering into his ear. The woman at the desk found it adorable, especially when Dean snatched up the key card to their room and headed to the elevator. Sam was grinning as they waited to reach their floor.

When the door opened and Sam lead them to their room, Dean was muttering under his breath about how much of a sap Sam was. By the time the door opened, Sam quickly shut his brother up by pushing him against the door, slotting their lips together...  The reaction was one that Sam would burn into his mind forever. Dean's eyes fluttered and he went boneless at the kiss, moaning under his breath as Sam took the lead, wrapping an arm around his waist and leading him further into the room.

"Just relax, Dean... Let me take care of you," Sam said gently, taking his time in undressing Dean, starting with his jacket. The shirt came next, and Sam let his eyes run over that tanned skin, wanting to count every freckle, to trace every scar. He had all the time tonight to do just that, but right now, he wanted to admire. He ran a hand down Dean's front, experimenting, taking his time. Thumbs brushing against Dean's nipples, Sam noted the way Dean shivered from the touch and those sensitive nubs hardened under his calloused fingers.

Hands falling down, he traced the zipper and slowly, ever so slowly pulled it down, undoing the button on his way. "Commando?" He wasn't surprised that Dean wasn't wearing any underwear.

"Shut up."

"Shut you up? I plan too."

Tugging the pants down, he noted the way Dean was twitching, an anxious look on his brothers face. It finally hit Sam that Dean was nervous about this. His normally cocky brother was avoiding eye contact, acting like this was-

"Is this your first time with a guy?" Sam asked, standing up and looking down at Dean, watching his expression go from anxious to annoyed.

"So what if it is? I can handle it."

“Hey, I’m not saying you can’t handle it. It’ll be fine.. I’ll take this slow.” Sam assured, shutting whatever protest Dean had with a simple kiss. He went back to undressing Dean, tugging off his boots and socks before finally pulling his pants off as well. Dean was bare and beautiful in front of him, all tanned skin littered in freckles and muscle. He quickly disposed of his own clothes, letting them fall uncaring to the ground before gently putting his hands on Dean’s waist, pushing him back onto the bed.

Immediately, Sam started exploring, tracing over every scar, his lips brushing against them. He knew every mark on Dean’s body, every scar. The one on his shoulder, from the claws of a vampire. Sam traced it with his tongue, delighting in the shivers it caused. Dean’s face was flushed and Sam couldn’t help but press kisses to his cheeks, wanting to suddenly find out just how far he could make that flush go. He could see that Dean was still tense about this, but Sam knew how to make it all better.

“Hands and knees, Dean.”

Dean raised an eyebrow, looking up at his brother in question but did as he was told, rolling onto his stomach and getting on his hands and knees. God, there were freckles everywhere, lining down his hips, onto his ass even. Sam traced his hands down his spine, kissing down and enjoying the way Dean shivered at the touch. One hand went to Dean’s neck, guiding his chest onto the bed so his back was bowed in a beautiful arch. “Stay like that.” An order, not a request. Sam knew exactly how Dean got off on being ordered, and he took advantage of that.

Once he was sure that Dean would stay like that, Sam brought his hands to Dean’s ass, massaging and just looking for a few moments. Finally, he parted his cheeks, looking at that hole. It was pink and tight, but by the end of tonight, it would be completely wrecked. “Take a picture, it lasts- Ah!” Sam quickly shut his brother up by putting his lips to that tight hole and sucking, earning the most delicious whimpers from his brother. He savored the taste, licking around the rim until it was twitching and Dean was trembling on the bed, loosening it up. Once he was sure Dean was ready, Sam slipped his tongue inside, licking and nibbling gently. With the noises Dean was making, Sam was tempted to do this all night.

He pulled away with one last lick, tasting Dean on his tongue and absolutely loving it. Dean tasted like oil, smelled so natural that Sam wanted to bury his face into his ass forever. He knew the best way to do this would be to get Dean off though. Easing Dean onto his back, Sam took sight of his flushed face, looking down to see his cock curled against his stomach and leaking from the tip. Leaning down, he took the tip of Dean’s cock into his mouth, sucking on the head. Dean’s hand flew to Sam’s hair, gripping it tightly as Sam slowly, expertly took him down and started sucking. Tongue tracing the veins, he hollowed his cheeks, one hand going down to play with Dean’s balls. Within minutes, Dean was coming undone, shooting his load into Sam’s mouth with a loud cry.

It was beautiful. Dean’s expression was dazed, his face flushed from the pleasure. His cock was limp on his thigh, a bit of come dripping down from the tip that Sam hadn’t swallowed. He was beautiful, and he was more than ready. There was lubricant in the drawer, and Sam took his time in warming it between his fingers. He peppered kisses up and down Dean’s chest, taking care of paying special attention to his brothers nipples, enjoying the moans it drew. “You’re doing so good, baby boy,” Sam said softly, smiling at the nickname that made his brother blush in embarrassment.

“Your hole is so small, Dean. By the end of the night, I’ll be opening you up on my cock, baby boy. You want that?” He asked, running a slicked up finger around the rim, watching as Dean nodded eagerly. One finger breached him slowly, and Sam hissed at how tight and hot Dean was around his finger. He couldn’t wait to get his dick inside. With Dean still relaxed from his orgasm, it didn’t take long before Sam was opening him up with a second finger, stretching him slowly, thrusting them in and out. He found that bundle of nerves soon enough, crooking his fingers into it and watching Dean’s reaction. Dean arched his back, hands gripping the blankets as he moaned, eyes rolling back in his head.

“There we are,” Sam murmured, alternating between rubbing his prostate and stretching him with two fingers. Soon, he was slick and open enough to add a third. Sam sat back as he watched the rim open up around his fingers, imagining how open Dean would be when he finally got his cock in there. Dean was writhing on his fingers soon enough, cock half hard and Sam thought it was enough. Dean was ready. Pulling his fingers out, Sam took the lubricant and slicked up his own hard cock, which he’d been neglecting in favor of making this good for Dean. It was Dean’s first time, and Sam was determined to make this a night to remember.

It would be easier for Dean on his stomach, but Sam wanted to see his brothers face. Spreading Dean’s legs, he gripped at his thighs, moving his brothers hands to hold his legs open. “Stay like that. Good boy.” Sam murmured, rubbing at his thigh gently. He guided his own slick cock to Dean’s hole, pushing patiently until the head popped inside. Even after all of that prep, Dean felt tight, heat clinging to his cock. They both moaned, and Sam managed to sink a few more inches in, never once taking his eyes off of Dean’s face, watching the emotions play over his face.

“Good boy, there we go,” Sam panted, gripping his hips as he thrust inside, sheathing himself fully inside. He had to keep himself from coming right there, gasping at how amazing it felt. Sam gave him a few minutes to get use to the stretch, looking down to where they were connected, one hand going down to trace the rim. It felt amazing, honestly, and Sam wanted to stay like this forever. He pulled out, leaving just the head of his cock inside before he thrust in, holding onto Dean tightly as he started at a slow pace.

“Fuck. Fuck, there we go. Good boy,” Sam panted, gripping Dean’s hips as he started thrusting harder. Dean was panting, his expression blissed out and so damned beautiful. Sam angled his hips so that every thrust was hitting his prostate, one hand going up to wrap around Dean’s leaking cock, stroking in time with his thrusts. Within a few minutes, Dean was yelling Sam’s name, crying out in pure pleasure as he came. The feeling of Dean tightening around his cock had Sam spilling over the edge and coming inside of Dean, his hips stuttering as he unloaded inside of him. He panted, pulling out after a few minutes, watching a mix of come and lube slide out of Dean’s ass. They were both covered in sweat, the scent of sex mixing in the air.

“Good boy,” Sam repeated, laying beside Dean and pulling his pliant body against his chest, holding him close. Dean would usually protest that he didn't need to cuddle, but this time he was curling against Sam’s chest, burying his face into his neck. “There we go. Was that good?” He asked softly.

“I... Sam, fuck,” Dean panted, looking up at Sam. “Fuck, you were right. That was good.”

“Good. Get some rest. Round two is going to start soon.” Sam said as he slapped Dean’s ass, smirking at the way the incredulous look he was given. “We have the room for two days, Dean. I intend to make the most of it.”


End file.
